Formaldehyde → HCID 15881114, compound

HRID 1461361Notes

Reaction equation

HRID 1461361 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][C:12]1([CH3:20])[O:19][C:17](=[O:18])[CH2:16][C:14](=[O:15])[O:13]1.N1CCC[C@H:22]1C(O)=O.C=O>C(#N)C>[CH3:11][C:12]1([CH3:20])[O:19][C:17](=[O:18])[CH:16]([CH2:22][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=3)[NH:7][CH:6]=2)[C:14](=[O:15])[O:13]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 249055-BromoindoleHCID 145742L-Proline

Product 1

HCID 15881114HCID 15881114, compoundYield 417.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-bromoindole (10.07 g, 51 mmol), Meldrum's acid (7.38 g, 51 mmol), proline (1.24 g), and 5.2 ml of 30% aqueous formaldehyde in 100 ml of acetonitrile was allowed to stand at room temperature for 24 hours. The acetonitrile was removed in vacuo. Crystallization of the product from methanol (50 ml) provided 15.83 g of 3-(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-yl)methyl-5-bromoindole as a white solid.

Workup

  1. customThe acetonitrile was removed in vacuo
  2. customCrystallization of the product from methanol (50 ml)

Sources & evidence

ORD record
ord-ae92c0f1983649649f18a011a7b183c9
Source dataset
uspto-grants-1991_12
Patent number
US05075313

Reaction notes

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